KR20150106501A - Compound and organic light emitting device comprising same - Google Patents

Abstract

Disclosed are a compound and an organic light emitting device including the same. The compound is represented by the chemical formula 1 below, wherein A refers to O or S; Ar_1 to Ar_4 refer to a substituted or unsubstituted aryl group, hetero-aryl group, or condensed multi-substituent; R_1 and R_2 refer to a substituted or unsubstituted alkyl group, aryl group, hetero-aryl group, or condensed multi-substituent; X and Y individually refer to a substituted or unsubstituted arylene group, hetero-arylene group, or condensed multi-substituent; and m and n individually refer to an integer of zero or one (excluding the case when both m and n refer to zero). For a description of the chemical formula 1, refer to the following detailed description of the invention.

Description

TECHNICAL FIELD The present invention relates to a compound and an organic light emitting device,

And an organic light emitting device including the same.

The organic light emitting device is a self light emitting type device having a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and multi-coloring.

A typical organic light emitting device may have a structure in which an anode is formed on a substrate, and a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially formed on the anode. Here, the hole transporting layer, the light emitting layer, and the electron transporting layer are organic thin films made of organic compounds.

The driving principle of the organic light emitting device having the above-described structure is as follows.

When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light emitting layer via the hole transporting layer, and electrons injected from the cathode move to the light emitting layer via the electron transporting layer. The carriers such as holes and electrons recombine in the light emitting layer region to generate an exiton. This exciton changes from the excited state to the ground state and light is generated.

There is a continuing demand for a material having an excellent electrical stability, a high charge transporting ability, or a light emitting ability, a high glass transition temperature and preventing crystallization as compared with conventional organic monomolecular materials.

High electrical conductivity, high charge transporting ability, high glass transition temperature and high crystallinity and is suitable for a fluorescent or phosphorescent device of all colors such as red, green, blue and white, and a high efficiency, low voltage , A high luminance, and a long life.

According to one aspect of the present invention, there is provided a compound represented by the following Formula 1:

≪ Formula 1 >

In Formula 1,

A represents O or S,

Ar ₁ to Ar ₄ each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, a substituted or unsubstituted condensed polycyclic group having 6 to 60 carbon atoms, And,

R ₁ and R ₂ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, A condensed polycyclic group having 6 to 60 carbon atoms,

X and Y are each independently a single bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 heteroarylene group; A substituted or unsubstituted condensed polycyclic group having 6 to 30 carbon atoms; Or a connecting group in which at least two of said arylene group, heteroarylene group and condensed polycyclic group are connected,

m and n each independently represent an integer of 0 or 1 (except when m and n are both 0).

According to another aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the compound.

According to another aspect of the present invention, there is provided a flat panel display device including the organic light emitting device, wherein a first electrode of the organic light emitting device is electrically connected to a source electrode or a drain electrode of the thin film transistor.

When the structure of Formula 1, which is a compound of the present invention, is used as a hole injecting layer or a hole transporting layer material, the driving voltage is lowered and the efficiency is increased compared with known compounds. In particular, it is possible to obtain an effect of increasing the half-life of luminance of the device.

1 is a schematic view showing the structure of an organic light emitting device according to an embodiment.

The compound according to one aspect of the present invention is represented by the following Formula 1:

≪ Formula 1 >

In Formula 1,

A represents O or S,

Ar ₁ to Ar ₄ each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, a substituted or unsubstituted condensed polycyclic group having 6 to 60 carbon atoms, And,

R ₁ and R ₂ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, A condensed polycyclic group having 6 to 60 carbon atoms,

X and Y are each independently a single bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 heteroarylene group; A substituted or unsubstituted condensed polycyclic group having 6 to 30 carbon atoms; Or a connecting group in which at least two of said arylene group, heteroarylene group and condensed polycyclic group are connected,

m and n each independently represent an integer of 0 or 1 (except when m and n are both 0).

The dibenzo xantene structure forming the central skeleton of the compound structure of the present invention has already been known for a long time. (Journal of the Chemical Society, Transactions, 1914, 399). Also, as an application of such a compound, there has been reported an example of using a structure such as BisN-1 shown below in WO02013 / 024779 as a film forming material for lithography, In JP5229521, an example using a polymer having the structure of the following formula (E) as an optical recording medium material has been reported.

But. There has been no report on the use of compounds having a monoarylamine or diarylamine as a substituent in the dibenzo xanthene skeleton of the present invention as an organic light emitting device.

Various types of arylamine compounds have been reported as hole injection and hole transport layer materials for organic light emitting devices and have been applied to actual devices.

Typical hole injecting and hole transporting layer materials include NPB compound structures disclosed by Kodak. Idemitsu's biphenyl-containing compounds and the following materials used in our company are typical compounds used in hole injection and transport layers. However, existing materials show excellent efficiency and lifetime characteristics when applied to organic light emitting devices. However, due to problems such as denaturation due to excessive thermal stress during deposition and various process problems due to melting of materials, Is required. In particular, it is necessary to develop a material having high heat resistance without denaturing the material even in a high temperature environment. In the present invention, a hole injection and hole transport layer material using a novel benzothane or benzothiocyanin compound is proposed, and a high efficiency, long life organic light emitting device is realized based on the thermal stability.

Materials having higher thermal durability can be obtained by appropriately modifying the substituents (for example, R ₁ , R ₂ , Ar ₁ -Ar _4, etc.) of Formula 1 of the embodiment of the present invention.

Particularly, introduction of an O or S atom into A of the structure of the above formula (1) can introduce an intramolecular non-conjugated pair, and when an electric field is formed in the organic light emitting device, resistance to holes injected from the anode is strengthened In addition, the ability to transport holes into surrounding molecules becomes even greater. Accordingly, when the compounds of the present invention are used as a hole injecting layer or a hole transporting layer compound in an organic light emitting device, the efficiency and lifetime of the device can be increased with higher hole transporting properties than conventional hole transporting materials.

The substituents of the above formula (1) will be described in more detail.

According to one embodiment of the present invention, R ₁ and R ₂ in Formula 1 may be connected to each other to form a saturated or unsaturated ring. In this case, the core of formula (1) becomes a spyro type.

According to another embodiment of the present invention, R ₁ and R ₂ in Formula 1 may be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or any of the following formulas (2a) to (2c):

Of the above formulas (2a) to (2c)

Z ₁ represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 20 carbon atoms, A condensed polycyclic group having 6 to 20 carbon atoms, a halogen group, a cyano group, a nitro group, a hydroxyl group or a carboxy group;

p is an integer from 1 to 7; * Represents the bond site.

According to another embodiment of the present invention, Ar ₁ to Ar ₄ in formula (1) may be any one of the following formulas (3a) to (3f):

Among the above-mentioned formulas (3a) to (3f)

Q ₁ is -C (R ₃₁ ) (R ₃₂ ) -, -O-, -S-, or -NR ₃₃ -;

Z ₁ and R ₃₁ to R ₃₃ independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group having 6 or more carbon atoms A substituted or unsubstituted C1 to C20 aryl group, a substituted or unsubstituted C6 to C20 arylsilyl group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C6 to C20 arylamino group, A substituted or unsubstituted, condensed polycyclic group having 6 to 20 carbon atoms, a halogen group, a cyano group, a nitro group, a hydroxyl group or a carboxy group;

p is an integer from 1 to 9; * Represents the bond site.

According to another embodiment of the present invention, X and Y in the formula (1) may be a direct bond or any one of the following formulas (4a) to (4e)

In the above formulas (4a) to (4e), * represents a bonding site.

According to another embodiment of the present invention, the formula 1 may be represented by the following formula 2, 3, 4, or 5:

(2)

(3)

≪ Formula 4 >

≪ Formula 5 >

The definitions of the substituents and symbols in the above formulas (2) to (5) are as described above.

Hereinafter, typical substituents among the substituents used in the present specification are as follows (the number of carbon atoms defining a substituent is not limited and the properties of the substituents are not limited, and the definition of substituents not defined herein is generic According to the definition).

An unsubstituted group having 1 to 60 carbon atoms Alkyl groups may be linear and branched and non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, heptyl, octyl, nonanyl, , At least one hydrogen atom of the alkyl group may be substituted with a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, 1 to 10 carbon atoms An alkyl group having 1 to 10 carbon atoms An alkoxy group having 2 to 10 carbon atoms An alkenyl group having 2 to 10 carbon atoms An alkynyl group, an aryl group having 6 to 16 carbon atoms, an aryl group having 4 to 16 carbon atoms A heteroaryl group, or an organosilyl group.

The unsubstituted alkenyl group having 2 to 60 carbon atoms means that at least one carbon double bond is contained at the middle or end of the unsubstituted alkyl group. Examples include ethenyl, propenyl, butenyl, and the like. At least one hydrogen atom in these unsubstituted alkenyl groups may be substituted with the same substituent as in the case of the substituted alkyl group described above.

An unsubstituted alkynyl group having 2 to 60 carbon atoms means that at least one carbon triple bond is contained at the middle or end of the alkyl group as defined above. Examples include acetylene, propylene, phenylacetylene, naphthylacetylene, isopropylacetylene, t-butylacetylene, diphenylacetylene, and the like. At least one hydrogen atom in these alkynyl groups may be substituted with the same substituent as in the case of the substituted alkyl group described above.

The unsubstituted cycloalkyl group having 3 to 60 carbon atoms means a cyclic alkyl group having 3 to 60 carbon atoms and at least one hydrogen atom in the cycloalkyl group may be substituted with the same substituent as the substituent group of the alkyl group having 1 to 60 carbon atoms Do.

The unsubstituted alkoxy group having 1 to 60 carbon atoms is preferably -OA, wherein A is an unsubstituted alkyl group having 1 to 60 carbon atoms Alkyl group), examples of which include, but are not limited to, methoxy, ethoxy, propoxy, isopropyloxy, butoxy, pentoxy, and the like. At least one hydrogen atom of these alkoxy groups may be substituted with the same substituent as in the case of the above-mentioned alkyl group.

An unsubstituted aryl group having 6 to 60 carbon atoms means a carbocyclic aromatic system containing at least one ring and may have two or more rings and may be fused with each other or connected via a single bond or the like. The term aryl includes aromatic systems such as phenyl, naphthyl, anthracenyl. At least one of the hydrogen atoms of the aryl group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms.

Examples of the substituted or unsubstituted aryl group having 6 to 60 carbon atoms include a phenyl group, (E.g., o-, m- and p-fluorophenyl groups, dichlorophenyl groups), cyanophenyl groups, dicyanophenyl groups, trifluoromethoxyphenyl groups, biphenyl groups , A halobiphenyl group, a cyanobiphenyl group, a group having 1 to 10 carbon atoms An alkylphenyl group, an alkylphenyl group having 1 to 10 carbon atoms M, and p-tolyl groups, o-, m-, and p-cumenyl groups, mesityl groups, phenoxyphenyl groups, (?,? - dimethylbenzene) phenyl groups, Naphthyl group, halonaphthyl group (for example, fluoronaphthyl group) having 1 to 10 carbon atoms, a monovalent group having 1 to 10 carbon atoms An alkylnaphthyl group (for example, methylnaphthyl group), a group of 1 to 10 carbon atoms An acenaphthyl group, a phenaranyl group, a fluorenyl group, an anthraquinolyl group, a methylene group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, A phenanthryl group, a triphenylene group, a pyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, A phenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, and an obarenyl group.

The unsubstituted heteroaryl group having 1 to 60 carbon atoms contains 1, 2, 3 or 4 hetero atoms selected from N, O, P or S, and when they have two or more rings, they may be fused with each other, Lt; / RTI > An unsubstituted group having 1 to 60 carbon atoms Examples of the heteroaryl group include a pyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, A benzoyl group, a carbazolyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, and a dibenzothiophen group. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms.

The unsubstituted aryloxy group having 6 to 60 carbon atoms is a group represented by -OA ₁ , wherein A ₁ is an aryl group having 6 to 60 carbon atoms. Examples of the aryloxy group include a phenoxy group and the like. At least one hydrogen atom of the aryloxy group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms.

The unsubstituted arylthio group having 6 to 60 carbon atoms is a group represented by -SA ₁ , wherein A ₁ is an aryl group having 6 to 60 carbon atoms. Examples of the arylthio group include a benzene thiol group and a naphthylthio group. At least one hydrogen atom of the arylthio group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms described above.

An unsubstituted C6-C60 The condensed polycyclic ring refers to a substituent containing two or more rings in which at least one aromatic ring and at least one non-aromatic ring are fused to each other or a substituent having an unsaturated group in the ring but not having a conjugated structure, Lt; RTI ID = 0.0 > and / or < / RTI > heteroaryl groups.

Specific examples of the compound represented by Formula 1 of the present invention include, but are not limited to, the following compounds.

An organic light emitting device according to another aspect of the present invention includes: a first electrode; A second electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a compound represented by Formula 1.

The organic layer includes a hole injection layer, a hole transport layer, a functional layer (hereinafter referred to as an "H-functional layer") having both a hole injection function and a hole transport function, a buffer layer, an electron blocking layer, (Hereinafter referred to as an "E-functional layer") having both a blocking layer, an electron transporting layer, an electron injecting layer, and an electron transporting function and an electron injecting function.

More specifically, the organic layer may be a hole injecting layer, a hole transporting layer, or a functional layer having both a hole injecting function and a hole transporting function. For example, the compound may be used in a hole injection layer or a hole transport layer.

According to an embodiment of the present invention, the organic layer may include at least one of an electron injecting layer, an electron transporting layer, a functional layer having both an electron injecting and electron transporting function, a light emitting layer, a hole injecting layer, a hole transporting layer, Functional layer, and the light-emitting layer may include an anthracene-based compound, an arylamine-based compound, or a styryl-based compound.

According to another embodiment of the present invention, the organic light emitting device may include a functional layer having an electron injecting layer, an electron transporting layer, an electron injecting and electron transporting function, a light emitting layer, a hole injecting layer, a hole transporting layer, And at least one layer of a red layer, a green layer, a blue layer, or a white layer of the light emitting layer may include a phosphorescent compound, and the hole injecting layer, the hole transporting layer, The functional layer having the transport function at the same time may further include a charge generating material. Meanwhile, the charge generating material may be a p-dopant, and the p-dopant may be a quinone derivative, a metal oxide, or a cyano group-containing compound.

According to another embodiment of the present invention, the organic layer includes an electron transporting layer, and the electron transporting layer may include a metal complex. The metal complex may be a Li complex.

In the present specification, the term "organic layer" refers to a single layer and / or a plurality of layers interposed between the first and second electrodes of the organic light emitting device.

1 schematically shows a cross-sectional view of an organic light emitting device according to an embodiment of the present invention. Hereinafter, a structure and a manufacturing method of an organic light emitting diode according to an embodiment of the present invention will be described with reference to FIG.

As the substrate (not shown), a substrate used in a typical organic light emitting device can be used. A glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling and waterproofness can be used.

The first electrode may be formed by providing a first electrode material on a substrate using a deposition method, a sputtering method, or the like. When the first electrode is an anode, the first electrode material may be selected from materials having a high work function to facilitate hole injection. The first electrode may be a reflective electrode or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity can be used. Alternatively, when magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium- One electrode may be formed as a reflective electrode.

The first electrode may have a single layer or two or more multi-layer structures. For example, the first electrode may have a three-layer structure of ITO / Ag / ITO, but the present invention is not limited thereto.

An organic layer is provided on the first electrode.

The organic layer may include a hole injecting layer, a hole transporting layer, a buffer layer (not shown), a light emitting layer, an electron transporting layer, or an electron injecting layer.

The hole injection layer (HIL) may be formed on the first electrode by various methods such as a vacuum deposition method, a spin coating method, a casting method, and an LB method.

When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, and the like. For example, About 500 ° C, a vacuum of about 10 ^-8 to about 10 ^-3 torr, and a deposition rate of about 0.01 to about 100 Å / sec.

When the hole injection layer is formed by the spin coating method, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, and the coating is performed at a coating rate of about 2000 rpm to about 5000 rpm The rate of heat treatment for removing the solvent after coating may be selected from the range of about 80 ° C to 200 ° C, but is not limited thereto.

As the hole injecting material, a compound according to one embodiment of the present invention or a known hole injecting material can be used. As the known hole injecting material, for example, N, N'-diphenyl-N, N ' (N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4,4'-diamine -tolyl-amino) -phenyl] -biphenyl-4,4'-diamine: DNTPD) and copper phthalocyanine, m-MTDATA [4,4 ', 4 "-tris (3-methylphenylphenylamino) triphenylamine] NPB (N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine), TDATA, , Poly (3,4-ethylenedioxythiophene) / poly (4-ethylenedioxythiophene) / PEDOT / PSS (polyaniline / dodecylbenzenesulfonic acid) Poly (4-styrenesulfonate), Pani / CSA (polyaniline / camphor sulfonic acid) or PANI / PSS (polyaniline) ) / Poly (4-styrene sulfonate)), but it not intended to be used and the like, limited to:

The thickness of the hole injection layer may be from about 100 A to about 10,000 A, for example, from about 100 A to about 1000 A. When the thickness of the hole injection layer satisfies the above-described range, satisfactory hole injection characteristics can be obtained without a substantial increase in drive voltage.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by various methods such as a vacuum deposition method, a spin coating method, a casting method, and an LB method. In the case of forming the hole transporting layer by the vacuum deposition method and the spinning method, the deposition conditions and the coating conditions vary depending on the compound to be used, but they can generally be selected from substantially the same range of conditions as the formation of the hole injection layer.

As the hole transporting material, a compound according to one embodiment of the present invention, or a known hole transporting material, can be used. Examples of the known hole transporting material include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'- Biphenyl] -4,4'-diamine (TPD), 4,4 ', 4 "-tris (N-carbazolyl) triphenylamine (4,4' carbazolyl) triphenylamine), NPB (N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine) And the like, but the present invention is not limited thereto.

The thickness of the hole transporting layer may be from about 50 Å to about 2000 Å, for example, from about 100 Å to about 1500 Å. When the thickness of the hole transporting layer satisfies the above-described range, satisfactory hole transporting characteristics can be obtained without substantially increasing the driving voltage.

The H-functional layer may include at least one of a hole injection layer material and a hole transport layer material as described above. The H-functional layer may have a thickness ranging from about 100 Å to about 10,000 Å, For example, from about 100 angstroms to about 1000 angstroms. When the thickness of the H-functional layer satisfies the above-described range, satisfactory hole injection and aqueous characteristics can be obtained without substantial increase in driving voltage.

At least one of the hole injection layer, the hole transport layer, and the H-functional layer may include at least one of a compound represented by the following Chemical Formula 300 and a compound represented by the following Chemical Formula 350:

≪ Formula 300 >

≪ EMI ID =

In the above formulas 300 and 350, Ar ₁₁ , Ar ₁₂ , Ar ₂₁ and Ar ₂₂ are, independently of each other, a substituted or unsubstituted C ₅ -C ₆₀ arylene group. For a description of Ar ₁₁ , Ar ₁₂ , Ar ₂₁ and Ar ₂₂ , refer to the detailed description of L ₁ above.

In Formula 300, e and f may be, independently of each other, an integer of 0 to 5, or 0, 1 or 2. For example, e may be 1 and f may be 0, but is not limited thereto.

In the above formulas 300 and 350, R ₅₁ to R ₅₈ , R ₆₁ to R ₆₉ and R ₇₁ and R ₇₂ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, Substituted or unsubstituted C ₁ -C ₆₀ alkyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkenyl groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted aryl groups, hwandoen C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₆₀ aryl group, a substituted Or an unsubstituted C ₅ -C ₆₀ aryloxy group, or a substituted or unsubstituted C ₅ -C ₆₀ arylthio group. For example, R ₅₁ to R ₅₈ , R ₆₁ to R _69, and R ₇₁ and R ₇₂ independently of each other represent hydrogen; heavy hydrogen; A halogen atom; A hydroxyl group; Cyano; A nitro group; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; C ₁ -C ₁₀ alkyl group (for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group and the like); A C ₁ -C ₁₀ alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, etc.); Heavy hydrogen, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or substituted by one or more of its salt and phosphoric acid or its salts and the C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group; A phenyl group; Naphthyl group; Anthryl group; A fluorenyl group; Pyrenyl; Heavy hydrogen, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group substituted with one or more of the phenyl group, a naphthyl group, an anthryl group, fluorenyl group and pi les group; But is not limited thereto.

In the general formula (300), R ₅₉ represents a phenyl group; Naphthyl group; Anthryl group; A biphenyl group; A pyridyl group; And a substituted or unsubstituted C ₁ -C ₆ alkyl group which may have a substituent selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, C ₂₀ alkyl group, and a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group substituted by one or more of the phenyl group, a naphthyl group, an anthryl group, a biphenyl group and a pyridyl group; ≪ / RTI >

According to one embodiment, the compound represented by Formula 300 may be represented by Formula 300A, but is not limited thereto:

≪ Formula 300A >

For details of R ₅₁ , R ₆₁ , R ₆₂ and R ₅₉ in the above formula (300A), refer to the above description.

For example, at least one of the hole injection layer, the hole transporting layer, and the H-functional layer may include at least one of the following compounds 301 to 320, but is not limited thereto:

At least one of the hole injecting layer, the hole transporting layer and the H-functional layer may be formed by a known hole injecting material, a known hole transporting material, and / or a material having both hole injecting and hole transporting functions, And the like. The charge-generating material may further include a charge-generating material.

The charge-producing material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracano-1,4-benzoquinone di Quinone derivatives such as phosphorus (F4-TCNQ); Metal oxides such as tungsten oxide and molybdenum oxide; And a cyano group-containing compound such as the following compound 200, but are not limited thereto.

<Compound 200> <F4-TCNQ>

When the hole-injecting layer, the hole-transporting layer, or the H-functional layer further comprises the charge-generating material, the charge-producing material is homogeneously (uniformly) injected into the hole-injecting layer, the hole- ) Dispersed, or non-uniformly distributed.

A buffer layer may be interposed between at least one of the hole injection layer, the hole transport layer, and the H-functional layer and the light emitting layer. The buffer layer may serve to increase the efficiency by compensating the optical resonance distance according to the wavelength of the light emitted from the light emitting layer. The buffer layer may include a known hole injecting material, a hole transporting material. Alternatively, the buffer layer may include one of the materials included in the hole injection layer, the hole transport layer, and the H-functional layer formed under the buffer layer.

Then, a light emitting layer (EML) can be formed on the hole transport layer, the H-functional layer, or the buffer layer by a method such as a vacuum evaporation method, a spin coating method, a casting method, or an LB method. When a light emitting layer is formed by a vacuum deposition method and a spin coating method, the deposition conditions vary depending on the compound used, but generally, the conditions can be selected from substantially the same range as the formation of the hole injection layer.

The light emitting layer may be formed using various known light emitting materials, and may be formed using known hosts and dopants. In the case of the above-mentioned dopant, a known fluorescent dopant and a known phosphorescent dopant can be used.

For example, known hosts include Alq ₃ , CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole) 2-yl) anthracene (ADN), TCTA, TPBI (1,3,5-tris (N-phenylbenzimidazole- ) benzene), TBADN (3-tert-butyl-9,10-di (naphth-2-yl) anthracene), E3, DSA (distyrylarylene), dmCBP 509, and the like may be used, but the present invention is not limited thereto.

     PVK       ADN

Alternatively, as the host, an anthracene-based compound represented by the following formula (400) can be used:

&Lt; Formula 400 >

In Formula 400, Ar ₁₁₁ and Ar ₁₁₂ are independently a substituted or unsubstituted C ₅ -C ₆₀ arylene group; Ar ₁₁₃ to Ar ₁₁₆ independently represent a substituted or unsubstituted C ₁ -C ₁₀ alkyl group or a substituted or unsubstituted C ₅ -C ₆₀ aryl group; g, h, i and j may be an integer of 0 to 4 independently of each other.

For example, in the general formula (400), Ar ₁₁₁ and Ar ₁₁₂ represent a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; Or a phenylene group, a naphthylene group, a phenanthrenylene group, a fluorenyl group, or a pyrenylene group substituted with at least one of a phenyl group, a naphthyl group and an anthryl group, but is not limited thereto.

G, h, i and j in Formula 400 may be independently 0, 1 or 2.

중 하나일 수 있으나, 이에 한정되는 것은 아니다.In Formula 400, Ar ₁₁₃ to Ar ₁₁₆ independently represent a C ₁ -C ₁₀ alkyl group substituted by at least one of a phenyl group, a naphthyl group, and an anthryl group; A phenyl group; Naphthyl group; Anthryl group; Pyrenyl; A phenanthrenyl group; A fluorenyl group; Heavy hydrogen, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ A phenyl group substituted by at least one of a C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group, A naphthyl group, an anthryl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group; And

But is not limited thereto.

For example, the anthracene-based compound represented by Formula 400 may be one of the following compounds, but is not limited thereto:

Alternatively, as the host, an anthracene-based compound represented by the following formula (401) can be used:

&Lt; Formula 401 >

Of the above formula 401, Ar ₁₂₂ To Ar &lt; ₁₂₅ &gt; refer to the description of Ar &lt; ₁₁₃ &gt; in the above formula (400).

Ar ₁₂₆ and Ar ₁₂₇ in Formula 401 may be, independently of each other, a C ₁ -C ₁₀ alkyl group (for example, a methyl group, an ethyl group or a propyl group).

K and l in Formula 401 may be independently an integer of 0 to 4. For example, k and l may be 0, 1 or 2.

For example, the anthracene-based compound represented by Formula 401 may be one of the following compounds, but is not limited thereto:

When the organic light emitting device is a full color organic light emitting device, the light emitting layer may be patterned as a red light emitting layer, a green light emitting layer, and a blue light emitting layer.

At least one of the red, green and blue luminescent layers may include one or more of the following dopants (ppy = phenylpyridine)

For example, as the blue dopant, the following compounds may be used, but the present invention is not limited thereto.

           DPAVBi

      TBPe

For example, the following compounds may be used as the red dopant, but the present invention is not limited thereto.

For example, the following compounds can be used as the green dopant, but the present invention is not limited thereto.

On the other hand, the dopant which may be included in the light emitting layer may be a complex as described below, but is not limited thereto:

In addition, the dopant that may be included in the light emitting layer may be Os-complex as described below, but is not limited thereto:

When the light emitting layer includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 15 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

The thickness of the light emitting layer may be about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer satisfies the above-described range, it is possible to exhibit excellent light-emitting characteristics without substantial increase in driving voltage.

Next, an electron transport layer (ETL) is formed on the light emitting layer by various methods such as a vacuum evaporation method, a spin coating method, and a casting method. When an electron transporting layer is formed by a vacuum deposition method and a spin coating method, the conditions vary depending on the compound used, but generally, the conditions can be selected from substantially the same range as the formation of the hole injection layer.

As the electron transporting layer material, a known electron transporting material can be used as a material that stably transports electrons injected from an electron injection electrode (cathode). Examples of known electron transporting materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10- olate: Bebq ₂ ), ADN, compound 201, compound 202, and the like may be used, but the present invention is not limited thereto.

<Compound 201> <Compound 202>

           BCP

The thickness of the electron transporting layer may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transporting layer satisfies the above-described range, satisfactory electron transporting characteristics can be obtained without substantially increasing the driving voltage.

Alternatively, the electron transporting layer may further include a metal-containing substance in addition to a known electron transporting organic compound.

The metal-containing material may comprise a Li complex. Non-limiting examples of the Li complex include lithium quinolate (LiQ), the following compound 203, and the like:

<Compound 203>

Further, an electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be laminated on the electron transporting layer, which is not particularly limited.

As the electron injection layer formation material, any material known as an electron injection layer formation material such as LiF, NaCl, CsF, Li ₂ O, BaO, or the like can be used. The deposition conditions of the electron injection layer may vary depending on the compound used, but may generally be selected from the same range of conditions as the formation of the hole injection layer.

The thickness of the electron injection layer may be from about 1 A to about 100 A, and from about 3 A to about 90 A. When the thickness of the electron injection layer satisfies the above-described range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

A second electrode is provided on the organic layer. The second electrode may be a cathode, which is an electron injection electrode. The metal for forming the second electrode may be a metal, an alloy, an electrically conductive compound, or a mixture thereof having a low work function. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- So that a transparent electrode can be obtained. On the other hand, in order to obtain a front light emitting element, a transparent electrode using ITO or IZO can be formed, and various modifications are possible.

The organic light emitting device has been described above with reference to FIG. 1, but the present invention is not limited thereto.

When a phosphorescent dopant is used for the light emitting layer, in order to prevent the triplet excitons or holes from diffusing into the electron transporting layer, a vacuum evaporation method, a spin coating method, a vacuum evaporation method, or a vacuum evaporation method may be used between the hole transporting layer and the light emitting layer, The hole blocking layer HBL can be formed by a method such as a casting method, an LB method, or the like. In the case of forming the hole blocking layer by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound used, but they can be generally within the same range of conditions as the formation of the hole injection layer. Known hole blocking materials can also be used. Examples thereof include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and the like. For example, the following BCP can be used as a hole blocking layer material.

The thickness of the hole blocking layer may be about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above-described range, excellent hole blocking characteristics can be obtained without increasing the driving voltage substantially.

The organic light emitting device according to the present invention may be provided in various types of flat panel display devices, for example, a passive matrix organic light emitting display device and an active matrix organic light emitting display device. In particular, in the case of the active matrix organic light emitting diode display, the first electrode provided on the substrate side may be electrically connected to the source electrode or the drain electrode of the thin film transistor as the pixel electrode. In addition, the organic light emitting device may be provided in a flat panel display device capable of displaying a screen on both sides.

Further, the organic layer of the organic light emitting device according to one embodiment of the present invention can be formed by a deposition method using a compound according to one embodiment of the present invention, or can be formed from a compound according to one embodiment of the present invention, Coating method.

Hereinafter, the organic light emitting device according to one embodiment of the present invention will be described in more detail with reference to the following Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples.

[Example]

Synthetic example  One:

(1) Synthesis of Intermediate 5-1

After methyl 2-bromo-5-chlorobenzoate (10 g) and 4-bromophenol (7 g) were diluted in pyridine (50 ml), K ₂ CO ₃ (8.3 g) and CuO (3.8 g) were added in this order, and the reaction mixture was stirred at 130 ° C for 5 hours. After cooling slowly at room temperature, the filtrate obtained after filtration under reduced pressure was conc. Neutralized with HCl and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 14 g of intermediate 5-1 quantitatively. The resulting compound was confirmed by LC-MS. _{(C 14 H 10 BrClO 3 M} + cal:. 339.95 found 339.97)

(2) Synthesis of intermediate 5-2

Intermediate 5-1 (14 g) was diluted with tetrahydrofuran (100 ml), and then methylmagnesium chloride (1M, 88 ml) was slowly added dropwise at -78 ° C. After maintaining the temperature at -78 ° C for 30 minutes, the temperature of the reaction mixture was slowly raised to room temperature, followed by stirring for 7 hours. The reaction was quenched with 1N HCl and extracted with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate, and the residue obtained by distillation under reduced pressure was separated and purified by silica gel column chromatography to obtain 14 g of intermediate 5-2 quantitatively. The resulting compound was confirmed by LC-MS. (C ₁₅ H ₁₄ BrCl ₂ M + cal.: 339.99 found 340.02)

(3) Intermediate 5-3

Intermediate 5-2 (14 g) was dissolved in dichloromethane (140 ml), followed by the addition of metal sulfonyl acid (0.1 ml). After 10 minutes, the reaction was terminated with triethylamine (1 ml), and the residue obtained by distillation under reduced pressure was purified by silica gel column chromatography to obtain intermediate 5-3 (9.8 g) in 76% yield. The resulting compound was confirmed by LC-MS. (C ₁₅ H ₁₂ BrClO M + cal.: 321.98 found 321.96)

(4) Synthesis of Compound 5

Pd (dba) ₃ (360 mg), P ( t- Bu) ₃ (1 M, 0.4 ml, ) And KOtBu (2.7 g) were dissolved in toluene (75 mL) and stirred at 85? For 2 hours. The reaction solution was quenched with water to room temperature and extracted three times with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain Compound 5 (5.3 g, yield 83%)

Synthetic example  2: Synthesis of Compound 19

Compound 19 (4.6 g, yield 86%) was obtained in the same manner as in compound 5 except that Intermediate 5-3 (3 g) and 4-fluoro-N-phenylamine (3.8 g) were used.

Synthetic example  3: Synthesis of Compound 38

Compound 38 (3.6 g, 91%) was prepared in the same manner as compound 5, except that Intermediate 5-3 (1.5 g) and di [(1,1'- ).

Synthetic example  4: Synthesis of Compound 42

The title compound was prepared following the procedure described for the synthesis of Compound 5, except that Intermediate 5-3 (1.5 g) and N - ([1,1'-biphenyl] -4-yl) dibenzo [b, d] furan- To give compound 42 (3.3 g, yield 81%).

Synthetic example  5: Synthesis of compound 47

Compound 47 (3.2 g) was obtained in the same manner as in the compound 5 except that Intermediate 5-3 (1.5 g) and N - ([1,1'-biphenyl] g, yield 86%).

Synthetic example  6:

(1) Synthesis of intermediate 52-1

Intermediate 52-1 (14g) was quantitatively obtained in the same manner as Intermediate 5-2 except that Intermediate 5-1 (10 g) and phenylmagnesium bromide (1M, 64.2 ml) were used. The resulting compound was confirmed by LC-MS. (C ₂₅ H ₁₈ BrClO ₂ M + cal.: 464.02 found 464.03)

(2) Synthesis of intermediate 52-2

Intermediate 52-2 (12 g, yield 88%) was obtained in the same manner as in the synthesis of intermediate 5-3 except that intermediate 52-1 (14g) was used. The resulting compound was confirmed by LC-MS. _{(C 25 H 10Br ClO M +} cal:. 446.01 found 446.05)

(3) Synthesis of Compound 52

Compound 52 (5.6 g, yield 86%) was obtained in the same manner as in the synthesis of Compound 38, except that Intermediate 52-2 (3 g) was used.

Synthetic example  7: Synthesis of Compound 63

Compound 63 (4.2 g, yield 81%) was obtained in the same manner as in the synthesis of Compound 52, except that Intermediate 52-2 (3 g) and N-phenylnaphthalen-1 -amine (3.2 g) were used.

Synthetic example  8:

(1) Synthesis of Intermediate 66-1

Intermediate 66-1 (14g) was quantitatively obtained in the same manner as in the synthesis of Intermediate 5-1 except that methyl 2-bromo-4-chlorobenzoate (10g) and 3-bromophenol (7g) were used . The resulting compound was confirmed by LC-MS. (C ₁₄ H ₁₁ ClO ₃ M + cal .: 262.04 found 262.07)

(2) Synthesis of intermediate 66-2

Intermediate 66-2 (14g) was quantitatively obtained in the same manner as in the synthesis of intermediate 5-2 except that intermediate 66-1 (14g) was used. The resulting compound was confirmed by LC-MS. (C ₁₅ H ₁₄ BrCl ₂ M + cal.: 339.99 found 340.02)

(3) Synthesis of intermediate 66-3

Intermediate 66-3 (10 g, 79%) was obtained in the same manner as in the synthesis of intermediate 5-3 except that intermediate 66-2 (14g) was used. The resulting compound was confirmed by LC-MS. (C ₁₅ H ₁₂ BrClO M + cal.: 321.98 found 321.99)

(4) Synthesis of Compound 66

Compound 66 (6.3 g, yield 81%) was obtained in the same manner as in the synthesis of Compound 5, except that di ([l, l'-biphenyl] -4- yl) amine (5.2 g) was used.

Synthetic example  9: Synthesis of Compound 70

Except using Intermediate 66-3 (1.5 g) and N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluoren- And the intermediate 70 (3.8 g, yield 88%) was obtained in the same manner as in the synthesis of intermediate 5.

Synthetic example  10:

(1) Synthesis of intermediate 87-1

The title compound was prepared in the same manner as the intermediate 5-1 except that methyl 2-bromobenzoate (10 g) and 4'-bromo- [1,1'-biphenyl] -4-ol (12 g) 87-1 (18 g) was quantitatively obtained. The resulting compound was confirmed by LC-MS. _{(C 20 H 15 BrO 3 M} + cal:. 382.02 found 382.03)

(2) Synthesis of intermediate 87-2

Intermediate 87-2 (18g) was quantitatively obtained in the same manner as Intermediate 5-2 except that Intermediate 87-1 (18g) was used. The resulting compound was confirmed by LC-MS. (C ₂₁ H ₁₉ Br _{2 2} + cal .: 382.06 found 382.09)

(3) Synthesis of intermediate 87-3

Intermediate 87-3 (14 g, yield 82%) was obtained in the same manner as Intermediate 5-3 except that Intermediate 87-2 (18 g) was used. The resulting compound was confirmed by LC-MS. _{(C21H 17 BrO M + cal:} . 364.05 found 364.06)

(4) Synthesis of Compound 87

Except using intermediate 87-3 (3g) and N - ([1,1'-biphenyl] -4-yl) -9,9-diphenyl-9H-fluorene- And Compound 87 (4.9 g, yield 77%) was obtained in the same manner as in the synthesis of Compound 5.

Synthetic example  11:

(1) Synthesis of intermediate 100-1

Intermediate 100-1 (11g) was quantitatively obtained in the same manner as in the synthesis of Intermediate 66-1 except that methyl 2-bromobenzoate (8g) was used. The resulting compound was confirmed by LC-MS. _{(C 14 H 11 BrO 3 M} + cal:. 305.99 found 305.98)

(2) Synthesis of intermediate 100-2

Intermediate 100-2 (16.7 g) was quantitatively obtained in the same manner as in the synthesis of Intermediate 57-1 except that Intermediate 100-1 (11g) was used. The resulting compound was confirmed by LC-MS. (C ₂₅ H ₁₈ BrClO ₂ M + cal.: 464.02 found 464.09)

(3) Synthesis of intermediate 100-3

Intermediate 100-3 (10.6 g, yield 68%) was obtained in the same manner as the synthesis of Intermediate 5-3 except that Intermediate 100-2 (16.7 g) was used. The resulting compound was confirmed by LC-MS. _{(C 25 H 17 BrO M +} cal:. 412.05 found 412.06)

(4) Synthesis of intermediate 100-4

3-iodo-9-phenyl -9 H - was dissolved carbazole (5g) and (4-bromophenyl) carbonyl Boro acid (2.7g) in tetrahydrofuran (50ml) and water (25ml), potassium carbonate ( 5.6 g) and Pd (PPh ₃ ) ₄ (780 mg) were added thereto and reacted at 65 ° C for 7 hours. The reaction mixture was slowly cooled to room temperature, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain Intermediate 100-4 (4.1 g, yield 76%) . The resulting compound was identified by LC-MS (C ₂₄ H ₁₆ BrN M + cal.: 397.05 found 397.06)

(5) Synthesis of 100-5

Intermediate 100-5 (4.6 g, yield 91%) was obtained in the same manner as in the synthesis of Compound 5, except that Intermediate 100-4 (4.1 g) and [1,1'-biphenyl] ). The resulting compound was confirmed by LC-MS. (C ₃₆ H ₂₆ N ₂ M + cal .: 486.21 found 486.23)

(6) Synthesis of Compound 100

Compound 100 (4.6 g, yield 77%) was obtained in the same manner as in the synthesis of Compound 5, except that Intermediate 100-3 (3 g) and Intermediate 100-5 (3.8 g) were used.

Synthetic example  12:

(1) Synthesis of intermediate 110-1

Intermediate 110-1 (14.4 g) was quantitatively obtained in the same manner as in the synthesis of Intermediate 5-1 except that 4-bromobenzothiol (7.6 g) was used. The resulting compound was confirmed by LC-MS. (C ₁₄ H ₁₀ BrClO ₂ S M + cal.: 355.93 found 355.96)

(2) Synthesis of intermediate 110-2

Intermediate 110-2 (19.3 g) was quantitatively obtained in the same manner as in the synthesis of Intermediate 52-1 except that Intermediate 110-1 (14.4 g) was used. The resulting compound was confirmed by LC-MS. (C ₂₅ H ₁₈ BrCl 3 M + cal.: 480.00 found 480.03)

(3) Synthesis of intermediate 107-3

Intermediate 107-3 (13.2 g, yield 71%) was obtained in the same manner as the synthesis of Intermediate 52-2 except that Intermediate 110-2 (19.3 g) was used. The resulting compound was confirmed by LC-MS. _{(C 25 H 16 BrClS M +} cal:. 461.98 found 461.99)

(4) Synthesis of Compound 110

Compound 110 (4.7 g, 74%) was obtained in the same manner as in the synthesis of Compound 52, except that Intermediate 110-3 (3g) was used.

NMR and mass data of the synthesized compounds are summarized in Table 1 below.

compound NMR H ¹ (CDCl _3, 400 MHz) LC / MS found calc. 5 2H), 7.08-7.04 (m, 4H), 6.77 (dd, 2H), 6.66-6.62 (m, 6H), 7.58-7.57 (m, 4H), 7.48-7.43 , 6.48-6.44 (m, 4H), 6.24-6.20 (m, 4H), 1.52 (s, 6H) 696.35 696.31 19 6H), 6.48-6.44 (m, 4H), 6.24-6.20 (m, 4H), 6.77 ), 1.52 (s, 6H) 580.28 580.23 38 2H), 6.67 (m, 4H), 6.54-6.50 (m, 8H), 7.58-7.54 (m, 8H), 7.48-7.43 1.52 (s, 6 H) 848.39 848.38 42 4H), 7.47-7.43 (m, 8H), 7.41-7.33 (m, 6H), 7.85-7.80 (m, 2H) ), 7.01 (dd, 2H), 6.83 (dd, 2H), 6.74-6. 72 (m, 2H), 6.64-6.56 876.36 876.34 47 2H), 7.32-7.21 (m, 4H), 7.48-7.41 (m, 10H) 6.75-6.63 (m, 8H), 6.36-6.32 (m, 4H), 1.52 (s, 6H) 796.37 796.35 52 7.48-7.43 (m, 16H), 7.38-7.36 (m, 4H), 7.26-7.22 (m, 8H), 7.17-7.14 (m, 2H), 6.84-6.67 , 4H), 6.66 (dd, 2H), 6.54-6.50 (m, 8H) 972.43 972.41 63 2H), 7.28-7.16 (m, 12H), 7.08-7.02 (m, 2H), 7.48 (d, 4H), 6.73 (dd, 2H), 6.65-6.54 (m, 4H), 6.19-6.13 (m, 8H)
768.33 768.31 66 2H), 6.46 (d, 2H), 6.67 (d, 2H), 6.67 (d, 2H), 7.58-7.57 (m, 8H), 7.47-7.43 6.29 (dd, 2H), 1.44 (s, 6H) 848.40 848.38 70 2H), 7.36-7.30 (m, 2H), 7.14-7.08 (m, 4H), 7.38-7.30 (m, 2H), 1.44 (s, 6H), 6.49 (d, 2H), 6.90 (d, 2H) 928.46 928.44 87 (M, 2H), 7.46-7.33 (m, 10H), 7.31-7.22 (m, 9H), 7.19-7.11 2H), 6.42 (d, 1H), 1.58 (s, 1H), 7.07 (dd, 6H) 769.35 769.33 100 (M, 8H), 7.38-7. 11 (m, 2H), 8.24 (d, 2H), 6.27-6.22 (m, 2H), 6.96 (d, 1H) 818.34 818.33 110 2H), 6.97 (d, 2H), 6.59 (d, 2H), 7.58-7.56 (m, 8H), 7.46-7.43 (m, 16H), 7.38-7.25 6.55-6.51 (m, 8H), 6.42 (dd, 2H) 988.43 988.39

Example  One

The anode Corning (corning) 15Ω / cm ² (1200 Å) ITO glass substrate was cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically washed with isopropyl alcohol and pure water for 5 minutes, exposed to ultraviolet rays for 30 minutes, exposed to ozone, cleaned, This glass substrate was provided.

Compound 5 of the present invention was vacuum deposited on the substrate to form a hole injection layer having a thickness of 600 Å. Then, 4,4'-bis [N- (1-naphthyl) N-phenylamino] biphenyl (hereinafter referred to as NPB) was vacuum-deposited to a thickness of 300 Å to form a hole transport layer.

On the upper side of the hole transport layer, a known blue fluorescent host  N, N ', N'-tetraphenyl-pyrene-1,6-diamine (TPD) as a blue fluorescent dopant and 9,10-di-naphthalene-2-yl-anthracene And a weight ratio of 98: 2 to form a light emitting layer having a thickness of 300 ANGSTROM.

Subsequently, an electron transport layer  Alq3 was deposited to a thickness of 300 angstroms. LiF, an alkali metal halide, was deposited on the electron transport layer to a thickness of 10 angstroms as an electron injection layer, and Al was vacuum deposited to a thickness of 3000 angstroms (cathode electrode) Thereby preparing an organic electroluminescent device.

Example  2

An organic EL device was fabricated in the same manner as in Example 1, except that Compound 19 was used instead of Compound 5 in forming the hole injection layer.

Example 3

An organic EL device was fabricated in the same manner as in Example 1, except that Compound 38 was used instead of Compound 5 in forming the hole injection layer.

Example 4

An organic EL device was fabricated in the same manner as in Example 1, except that Compound 42 was used instead of Compound 5 in forming the hole injection layer.

Example 5

An organic EL device was fabricated in the same manner as in Example 1, except that the known compound 2-TNATA was used instead of the compound 14 and the compound 47 of the present invention was used instead of NPB in the formation of the hole transport layer .

Example 6

An organic EL device was fabricated in the same manner as in Example 5, except that Compound 52 was used instead of Compound 47 in forming the hole transport layer.

Example 7

An organic EL device was fabricated in the same manner as in Example 5, except that Compound 63 was used instead of Compound 47 in forming the hole transport layer.

Example 8

An organic EL device was fabricated in the same manner as in Example 5, except that Compound 66 was used instead of Compound 47 in forming the hole transport layer.

Example 9

An organic EL device was produced in the same manner as in Example 5, except that Compound 70 was used instead of Compound 47 in forming the hole transport layer.

Example 10

An organic EL device was fabricated in the same manner as in Example 5, except that Compound 87 was used instead of Compound 47 in forming the hole transport layer.

Example 11

An organic EL device was fabricated in the same manner as in Example 5 except that Compound 97 was used instead of Compound 47 in forming the hole transport layer.

Example 12

An organic EL device was fabricated in the same manner as in Example 5, except that Compound 107 was used instead of Compound 47 in forming the hole transport layer.

Comparative Example  One

An organic EL device was fabricated in the same manner as in Example 1, except that 2-TNATA, which is a known compound, was used to form the hole injection layer.

The results of the above Comparative Examples and Examples are summarized in Table 2.

Hole injection or transport layer Driving voltage
(V) Current density
(MA / cm2) Luminance
(cd / m 2) efficiency
(cd / A) Luminous color Half life (hr @ 100 mA / cm 2) Example 1 Compound 5 5.63 50 3160 6.32 blue 346hr Example 2 Compound 19 5.46 50 3095 6.19 blue 309hr Example 3 Compound 38 5.52 50 3185 6.37 blue 342 hr Example 4 Compound 42 5.59 50 3175 6.35 blue 336hr Example 5 Compound 47 5.69 50 3210 6.42 blue 329hr Example 6 Compound 52 5.71 50 3260 6.52 blue 348 hr Example 7 Compound 63 5.67 50 3245 6.49 blue 329hr Example 8 Compound 66 5.65 50 3305 6.61 blue 351 hr Example 9 Compound 70 5.61 50 3345 6.69 blue 368hr Example 10 Compound 87 5.64 50 3295 6.59 blue 356 hr Example 11 Compound 97 5.66 50 3310 6.62 blue 379hr Example 12 Compound 107 5.68 50 3215 6.43 blue 329hr Comparative Example 1 2-TNATA 7.01 50 2645 5.29 blue 258hr

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. . Accordingly, the true scope of the present invention should be determined by the technical idea of the appended claims.

Claims (20)

A compound represented by the following formula (1):
&Lt; Formula 1 >

In Formula 1,
A represents O or S,
Ar ₁ to Ar ₄ each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, a substituted or unsubstituted condensed polycyclic group having 6 to 60 carbon atoms, And,
R ₁ and R ₂ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, A condensed polycyclic group having 6 to 60 carbon atoms,
X and Y are each independently a single bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 heteroarylene group; A substituted or unsubstituted condensed polycyclic group having 6 to 30 carbon atoms; Or a connecting group in which at least two of said arylene group, heteroarylene group and condensed polycyclic group are connected,
m and n each independently represent an integer of 0 or 1 (except when m and n are both 0). The method according to claim 1,
R ₁ and R ₂ are connected to form a saturated or unsaturated ring. The method according to claim 1,
R ₁ and R ₂ are each a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a group represented by any of the following formulas (2a) to (2c):

Of the above formulas (2a) to (2c)
Z ₁ represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 20 carbon atoms, A condensed polycyclic group having 6 to 20 carbon atoms, a halogen group, a cyano group, a nitro group, a hydroxyl group or a carboxy group;
p is an integer from 1 to 7;
* Represents the bond site. The method according to claim 1,
Ar &_lt; ₁ &gt; to Ar &_lt; ₄ &gt; are any one of the following formulas (3a) to

Among the above-mentioned formulas (3a) to (3f)
Q ₁ is -C (R ₃₁ ) (R ₃₂ ) -, -O-, -S-, or -NR ₃₃ -;
Z ₁ and R ₃₁ to R ₃₃ independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group having 6 or more carbon atoms A substituted or unsubstituted C1 to C20 aryl group, a substituted or unsubstituted C6 to C20 arylsilyl group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C6 to C20 arylamino group, A substituted or unsubstituted, condensed polycyclic group having 6 to 20 carbon atoms, a halogen group, a cyano group, a nitro group, a hydroxyl group or a carboxy group;
p is an integer from 1 to 9;
* Represents the bond site. The method according to claim 1,
X and Y are a direct bond, or a compound represented by any one of the following formulas (4a) to (4e):

In the above formulas (4a) to (4e), * represents a bonding site. The method according to claim 1,
Wherein the compound of Formula 1 is a compound of Formula 2:
(2)

The definition of the substituents and symbols in the above formula (2) is the same as in the above. The method according to claim 1,
Wherein the compound represented by Formula 1 is a compound represented by Formula 3:
(3)

The definitions of the substituents and symbols in the above formula (3) are the same as those in the above item (1). The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by Formula 4:
&Lt; Formula 4 >

The definitions of the substituents and symbols in the formula (4) are the same as in the above. The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by Formula 5:
&Lt; Formula 5 >

The definitions of the substituents and symbols in the above formula (5) are the same as in the above. The method according to claim 1,
Wherein the compound of Formula 1 is any one of the following compounds:

A first electrode;
A second electrode; And
An organic layer interposed between the first electrode and the second electrode,
Wherein the organic layer comprises the compound of claim 1. 10. The method of claim 9,
Wherein the organic layer is a hole injecting layer, a hole transporting layer, or a functional layer having both a hole injecting function and a hole transporting function at the same time. 12. The method of claim 11,
Wherein the organic layer includes a functional layer having a light emitting layer, an electron injecting layer, an electron transporting layer, a functional layer having both an electron injecting and electron transporting function, a hole injecting layer, a hole transporting layer,
Wherein the light emitting layer comprises an anthracene compound, an arylamine compound, or a styryl compound. 12. The method of claim 11,
Wherein the organic layer includes a functional layer having a light emitting layer, an electron injecting layer, an electron transporting layer, a functional layer having both an electron injecting and electron transporting function, a hole injecting layer, a hole transporting layer,
Wherein at least one of the red layer, green layer, blue layer or white layer of the light emitting layer comprises a phosphorescent compound. 12. The method of claim 11,
Wherein the organic layer comprises an electron transporting layer, and the electron transporting layer comprises a metal complex. 16. The method of claim 15,
Wherein the metal complex is a Li complex. 16. The method of claim 15,
Wherein the metal complex is lithium quinolate (LiQ). 16. The method of claim 15,
Wherein the metal complex is the following compound (203).
<Compound 203>

12. The method of claim 11,
Wherein the compound contained in the organic layer is formed through a wet process. The flat panel display device of claim 11, wherein the first electrode of the organic light emitting device is electrically connected to a source electrode or a drain electrode of the thin film transistor.

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